Classifications

• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
  • C09B1/16—Amino-anthraquinones
  • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
  • C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
  • C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
  • C09B1/16—Amino-anthraquinones
  • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
  • C09B1/36—Dyes with acylated amino groups
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
  • C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
  • C09B1/51—N-substituted amino-hydroxy anthraquinone
  • C09B1/514—N-aryl derivatives
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
  • Y10S8/908—Anionic emulsifiers for dyeing
  • Y10S8/912—Arylene sulfonate-formaldehyde condensate or alkyl aryl sulfonate
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
  • Y10S8/92—Synthetic fiber dyeing
  • Y10S8/922—Polyester fiber
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
  • Y10S8/933—Thermosol dyeing, thermofixation or dry heat fixation or development

Definitions

• acylpheuylaminoanthraquinones disclosed herein for use of dyestuffs for polyester fibrous materials are novel compounds and the preparation and use of these novel compounds are specifically disclosed herein.
• X is methoxy and one of Y or Z is methoxy and the other is II C-R where R has the meaning given above, the phenyl ring, A, can be substituted by halogen, hydroxy, lower alkyl or lower alkoxy; and with the proviso that only one of X, Y or Z can be the group Among the compounds of interest as dyestuffs for polyester fibrous materials, the following are of particular interest:
• acylphenylaminoanthraquinones employed according to the present invention are obtained as follows:
• An anthraquinone derivative containing at least one primary amino group is reacted with a halogenated com-pound such as p-chlorobenzaldehyde, p-bromobenzaldehyde, p chloroacetophenone, p bromoacetophenone, p-chlorobenzophenone, p bromobenzophenone or p-chloropropiophenone.
• a halogenated com-pound such as p-chlorobenzaldehyde, p-bromobenzaldehyde, p chloroacetophenone, p bromoacetophenone, p-chlorobenzophenone, p bromobenzophenone or p-chloropropiophenone.
• a halogenated com-pound such as p-chlorobenzaldehyde, p-bromobenzaldehyde, p chloroacetophenone,
• a chloroanthraquinone is reacted with a metaor para-aminophenylketone, such as metaor para-aminoacetophenone.
• the chloroanthraquinone can be l-chloroanthraquinone, 1-4-dichloroanthraquinone, 1,5-dichloro-4,8 dihydroxy anthraquinone, 1 methylamino-4-bromoanthraquinone or 1 amino 2 dibromoanthraquinone.
• a metaor para-aminophenylketone is condensed with dinitrochrysazin or dinitroanthrarufin in a suitable solvent, such as nitrobenzene, methylcellosolve, ethylcellosolve or amyl alcohol.
• a mixture of leuco-l,4,5,S-tetrahydroxyanthraquinone and boric acid is heated with a metaor para-aminophenylketone, such as metaor para-aminoacetophenone in an alcohol solvent, such as n-butyl alcohol or amyl alcohol.
• a metaor para-aminophenylketone such as metaor para-aminoacetophenone
• an alcohol solvent such as n-butyl alcohol or amyl alcohol.
• the said dyestuffs are preferably used in a finely divided form and the dyeing is carried out in the presence of a dispersing agent, such as sulphite cellulose waste liquor or a synthetic detergent, or a combination of different wetting and dispersing agents.
• a dispersing agent such as sulphite cellulose waste liquor or a synthetic detergent, or a combination of different wetting and dispersing agents.
• Dyestuff reparations of this kind can be made by known methods, for example, by grinding the dyestuif(s) either in dry or wet form with or without the addition of a dispersing agent.
• the dyestuffs used in the invention are especially suitable for dyeing by the so-called thermofixation or Pad/ Thermofix method, in which the fabric to be dyed is impregnated advantageously at a temperature not exceeding 60 C. with an aqueous dispersion of the dyestutf, which may contain 1 to 50% of urea and a thickening agent, especially sodium alginate, and the fabric is squeezed in the usual manner.
• the squeezing is preferably carried out so that the goods retain 50 to 100% of their weight of dye liquor.
• the dyestuff is fixed by subjecting the impregnated fabric to a heat treatment at temperatures above 100 C., for example, at a temperature ranging from 120-220 C., it being of advantage to dry the fabric prior to this treatment, for example, in a current of warm air.
• the padding liquor contains a dyestutf suitable for dyeing cotton, for example, a direct dyestuif or vat dyestuff, or a so-called reactive dyestufl, i.e. a dyestutf capable of being fixed on cellulose fibers with the formation of a chemical bond, for example, a dyestuff containing a chlorotriazine or chlorodiazine residue.
• a dyestutf suitable for dyeing cotton for example, a direct dyestuif or vat dyestuff, or a so-called reactive dyestufl, i.e. a dyestutf capable of being fixed on cellulose fibers with the formation of a chemical bond, for example, a dyestuff containing a chlorotriazine or chlorodiazine residue.
• an agent capable of binding acid for example, an alkali carbonate, alkali phosphate, alkali borate or alkali perborate, or a mixture of two or more of these agents.
• an agent capable of binding acid for example, an alkali carbonate, alkali phosphate, alkali borate or alkali perborate, or a mixture of two or more of these agents.
• the dyeings produced on polyester fibers by the process of the invention are advantageously given an after-treatment, for example, by heating them with an aqueous solution of a non-ionic detergent.
• the dyestuffs may be applied by printing.
• a printing color which, in addition to the usual printing assistants, such as wetting and thickening agents, contains the finely dispersed dyestuff, if desired, in admixture with one of the aforesaid cotton dyestuffs, and, if desired, in the presence of urea and/or an agent capable of binding acid.
• polyester defines synthetic polymeric polyesters, such as the highly polymeric linear polyesters, the molecules of which have recurring monomeric units connected by ester linkages.
• Dibasic acids for example, aromatic acids, such as terephthalic acid, diphenyl-4,4-dicar boxylic acid and/ or diphenyl-sulfone 4,4 -dicarboxylic acid and dihydroxy compounds, for example, glycols, such as ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol and/or butylene glycol, as well as other diols, such as 1,4-cyclohexyldiol can be used as the monomers to form the polymeric polyesters.
• Typical commercial examples of such fibers are Dacron, Terylene, Fortrel, Trevira, Terlanca, Kodel, Vycron, etc. They are disclosed, for example, in U.S. Patent No. 2,901,466 and British Patents Nos. 578,079, 579,462, 588,497, and 596,688.
• the present invention is, of course, equally applicable to the dyeing of blends of polyester fibers and cellulosic fibers.
• the latter term includes native cellulose, such as linen or, more particularly, cotton, as well as regenerated cellulose, such as viscose of cuprammonium rayon.
• EXAMPLE 1 60 parts of l,4-diaminoanthraquinone, 150 parts of 4- bromobenzophenone, parts of potassium acetate, 5 parts of cuprous chloride and 1400 parts of nitrobenzene are stirred and heated for 5 hours at 198-206 C. The mixture is cooled to 25-30 C., and the precipitated product is recovered by filtration. The product is washed with nitrobenzene and the nitrobenzene is then removed by steam distillation. Undissolved copper is solubilized by adding hydrochloric acid and the product is again recovered by filtration. 1
• the product, obtained as a presscake is 1,4-bis-p-benzoyl-anilinoanthraquinone.
• the presscake is converted to an aqueous paste by milling it with sodium lignin sulfonate.
• This paste dyes polyester fabrics by the Thermosol process a bright, deep green shade with excellent sublimation fastness and good light fastness.
• 1-hydroxy-4-m-benzoylanilinoanthraquinone is obtained as a dark, violet powder in a yield of 27.0; parts. When' used in dyeing, it gives violet dyeings having excellent light and sublimation fastness on polyester fibers.
• reaction mixture is then refluxed (132-134 C.), with stirring, for hours.
• the mixture is cooled to room temperature and filtered.
• the filtered product is washed three times with parts and converted to an aqueous paste as described in Example 1.
• the product l-hydroxy 4 p-benzolanilinoanthraquinone, gives violet dyeings on polyester fiber, possessing excellent fastness properties.
• EXAMPLE 6 160.0 parts of 95% ethyl alcohol and 30.0 parts of 70 anhydrous boric acid are heated together to reflux, with stirring, to dissolve the boric acid. 16.0 parts of Ieueoquinizarin, 37.0 parts of 5,8-dichloroquinizarin, and 28.0 parts of 3'-aminoacefophenone are added to the reaction ring, for 24-30 hours, 80.0 parts of ethyl alcohol is then added and the mixture is cooled and filtered. The filtered product is washed with 2X 50.0 parts of ethyl alcohol then with hot water followed by drying.
• the product consisting essentially of a mixture of 1-hydr0xy-4-m-acetylanilino-5,8-dichloroanthraquinone and 1 hydroxy-4-macetylanilinoanthraquinone, is obtained as a dark powder mixture.
• the reaction mixture is then refluxed, with stir- 75 in a yield of 69.0 parts.
• the product dyed polyester fibers in reddish blue shades; the dyeings exhibited excellent lightand sublimation fastness.
• EXAMPLE 8 17.9 parts of 1-hydroxy-4-m-acety1anilinoanthraquinone 3.6 parts of 4,5-dinitrochrysazin, 3.6 parts of p-amino- (Table III) and 400 parts o-dichl orobenzene are stirred u-hydroxyacetophenone and 54 parts of methyl cellosolve isstirred and refluxed for 18 hours. The reaction mixture isf'cooled to 25 C. and 50 parts of 5% hydrochloric acid solution is added during /2 hour. The slurry is stirred /2 hour, filtered and washed neutral.
• This dyestuff is essentially l,8dihydroxy-4-nitro-5-p-(ahydroxyacetylanilino)- anthraquinone.
• Amounts of this preparation sufficient to provide a concentration of 1.5, 3.0 and 6.0 parts of dyestuff per liter of dyebath, are' finely dispersed in water containing 10.0 parts of sodium alginate per liter and the resultant pad liquor is brought to a temperature of 25 C.
• Polyethylene terephthalate fabric is then padded with the above liquor and mechanicaly squeezed to a 65% pickup.
• the padded material is then air dried and developed by dry heat curing in an electrically heated, hot-air dryer for '1 minute at 200 C.
• the dyed fabric is scoured for minutes at the boil in a solution containing 3% of sodium di-iso-butyl naphthalene monosulfonate and 5% sodium carbonate and then dried.
• a bright blue-green dyeing is obtained characterized by excellent fastness to light and good sublimation fastness.
• X, Y and Z have the following relationships: (a) X, Y and Z are independently selected from the group consisting of hydrogen and hydroxyl, (b) one of X, Y and Z is a member selected from the group consisting of benzamido, p-toluenesulfonamido, benzenesulfonamido, hydroxy,
• R (d) X is methoxy, one of Y and Z is methoxy and the other is a member selected from the group consisting of 0 ll C-R NI-I- A with the proviso that only one of X, Y and Z can be and the phenyl ring A can be substituted by a member selected from the group consisting of halogen, hydroxy, lower alkyl and lower alkoxy.
• Linear polyester fibers according to claim 1 wherein the compound is O OH 3. Linear polyester fibers according to claim 1 wherein the compound is NH- COH3 4. Linear polyester fibers according to claim 1 wherein the compound is H 0 NH 5. Linear polyester fibers according to claim 1 wherein the compound is Hell 6. Linear polyester fibers according to claim 1 wherein the compound is UNITED STATES PATENTS 2,335,412 11/1943 Hentrich et a1. 260372 3,232,927 2/1966 Randall et a1. 260372 X FOREIGN PATENTS 391,930 9/1965 Switzerland.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
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• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

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Cited By (10)

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Citations (3)

• 1966
  • 1966-09-27 US US582222A patent/US3507606A/en not_active Expired - Lifetime
• 1967
  • 1967-09-16 DE DE19671619646 patent/DE1619646A1/de active Pending
  • 1967-09-25 CH CH1337167D patent/CH1337167A4/xx unknown
  • 1967-09-25 CH CH1337167A patent/CH492073A/de not_active IP Right Cessation
  • 1967-09-26 FR FR1552923D patent/FR1552923A/fr not_active Expired
  • 1967-09-26 ES ES345478A patent/ES345478A1/es not_active Expired
  • 1967-09-27 GB GB43922/67A patent/GB1172601A/en not_active Expired

Patent Citations (3)

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